Windsor vacation rentals

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Top-rated vacation rentals in Windsor

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Guesthouse in Sebastopol

4.93 out of 5 average rating, 674 reviews

Sun Drenched Flat

Put up the burnt-orange parasol and settle down with book on the patio while the barbecue heats up. Sitting above a garage in a serene, walkable neighborhood, this sunlit retreat's beachy cream painted paneling gives it a chilled, refined vibe. Check out all that Sebastopol has to offer at: visitsebastopolnow.come This second story house is a very desirable space, located close to town, still being set on a very beautiful street in an friendly established older neighborhood. It is nestled between other structures on the property. One being a "Tiny House" that is right next door, my home sits behind the flat. The house has a full kitchen with all the utensils and necessary cooking items, pots pans etc. Large toaster oven that will even fit your frozen pizza. There is a space in front with some Adirondack chairs and BBQ if you want to relax outside. The house has its own separate entrance off the driveway. My house is in back of the flat, I may or may not see you, but I am available for any questions at any time. You will more than likely be greeted by our white cat with orange tips (named White Boy). If he gets a chance, Charlie our very exuberant Golden Doodle will give you a warm excited welcome. Located just 1 mile from the heart of the sweet town of Sebastopol, this area is a handy stepping off point to explore nearby wineries, scenic beaches, and shopping and restaurants at redwoods. A very nice mile walk to town or a five minute drive. There is a flight of stairs that you climb to get to the Flat space, it does not have wheelchair access. There are cats on the property, but they do not go inside the flat. Our Goldendoodle is extremely friendly. The leather couch folds flat into a double bed for accommodating two more guests. Access to the bathroom is through the bedroom however. There is no dedicated parking, however the street parking directly across from the flat, just up from, but not in front of the three mailboxes is usually always open.

Jul 1 – 8

$120 per night
Guest favorite

Guest suite in Windsor

4.98 out of 5 average rating, 356 reviews

Private Entrance Suite in Heart of Wine Country

Situated in an upscale neighborhood, this exquisite guest suite boasts a private entrance on a safe, quiet cul-de-sac in the heart of the wine country. The en-suite is perfect for a romantic getaway, comfortable for an infant or small child, and ideal for the business traveler. We are 5 miles from Healdsburg and 3 from the Sonoma Co. Airport. Three parks within 4 miles encompass over 20 miles of hiking/biking. The Russian River, Redwoods, and Sonoma Coast are only a short, panoramic drive away.

Aug 12 – 19

$111 per night
Guest favorite

Home in Windsor

4.99 out of 5 average rating, 101 reviews

Gorgeous Victorian in the HEART of Windsor

Gorgeous renovated Queen Anne Victorian located in the heart of Windsor, CA combines quality finishes, modern convenience & vintage details. With a stylish kitchen, high ceilings, 3 beds/2 baths on a single level, HVAC & a huge lot with a Bocce Court. Walking distance to the Town Green, restaurants, wine tasting rooms and shopping. Just 3.5 miles from the Sonoma County Airport (STS), 5 miles to downtown Healdsburg, in the heart of the Russian River Valley & just 57 miles from the Golden Gate.

Sep 6 – 13

$394 per night

Popular amenities for Windsor vacation rentals

Stay near Windsor's top sights

Sonoma County Airport28 locals recommend
Windsor Town Green34 locals recommend
Riverfront Regional Park34 locals recommend
Airport Stadium 1221 locals recommend
Kendall-Jackson Wine Estate & Gardens46 locals recommend
KC's American Kitchen23 locals recommend

Other great vacation rentals in Windsor

Guest favorite

Guesthouse in Healdsburg

4.98 out of 5 average rating, 246 reviews

Alexander Valley: Wine Lover and Cycling Paradise

Sep 2 – 9

$164 per night
Guest favorite

Cottage in Windsor

5.0 out of 5 average rating, 117 reviews

Vineyard Cozy Cottage & Hot Tub

Dec 20 – 27

$202 per night
Guest favorite

Home in Santa Rosa

4.89 out of 5 average rating, 227 reviews

Sunshine cottage

Sep 24 – Oct 1

$135 per night
Guest favorite

Guesthouse in Sebastopol

4.98 out of 5 average rating, 428 reviews

Modern Bungalow Downtown Sebastopol

Jul 20 – 27

$100 per night
Guest favorite

Farm stay in Healdsburg

4.97 out of 5 average rating, 470 reviews

Gracianna Winery Vineyard Loft - Farm Stay

Mar 9 – 16

$263 per night
Guest favorite

Guest suite in Santa Rosa

4.91 out of 5 average rating, 245 reviews

Peaceful Wine Country Retreat / PRIVATE ENTRANCE

Nov 11 – 18

$118 per night
Superhost

Villa in Healdsburg

4.94 out of 5 average rating, 108 reviews

Hilltop Vista Villa

Dec 30 – Jan 6

$393 per night
Guest favorite

Apartment in Sebastopol

4.99 out of 5 average rating, 601 reviews

Amy's Local BNB - walk to town **and hot tub!**

Aug 21 – 28

$134 per night
Guest favorite

Home in Healdsburg

4.96 out of 5 average rating, 429 reviews

Dry Creek Valley Cottage

Mar 26 – Apr 2

$172 per night
Guest favorite

Guesthouse in Santa Rosa

4.96 out of 5 average rating, 168 reviews

KV garden Cottage.

Oct 28 – Nov 4

$104 per night
Guest favorite

Home in Windsor

4.93 out of 5 average rating, 147 reviews

Luxurious home and pool

Oct 31 – Nov 7

$495 per night
Guest favorite

Guest suite in Graton

4.95 out of 5 average rating, 261 reviews

The Flying Pig

Sep 13 – 20

$87 per night

Other great vacation rentals in Windsor

Guest favorite

Guest suite in Santa Rosa

4.97 out of 5 average rating, 179 reviews

Wine Country Retreat

Jan 5 – 12

$125 per night
Guest favorite

Guesthouse in Sebastopol

4.9 out of 5 average rating, 1107 reviews

Lemon Moon Cottage

Feb 9 – 14

$129 per night
Guest favorite

Guesthouse in Healdsburg

5.0 out of 5 average rating, 100 reviews

Luxe Guest Suite in Dry Creek 5 mins From Town!

Dec 18 – 25

$511 per night
Guest favorite

Guesthouse in Sebastopol

4.96 out of 5 average rating, 289 reviews

Arbor View

Jun 18 – 25

$106 per night
Guest favorite

Home in Healdsburg

4.93 out of 5 average rating, 522 reviews

Healdsburg Garden House

Nov 25 – Dec 2

$197 per night
Guest favorite

Guesthouse in Santa Rosa

4.89 out of 5 average rating, 259 reviews

Central Santa Rosa Garden Getaway

Jul 2 – 9

$103 per night
Guest favorite

Home in Cazadero

4.95 out of 5 average rating, 114 reviews

Ranch Stay for 2

Jan 19 – 26

$113 per night
Guest favorite

Guest suite in Santa Rosa

4.94 out of 5 average rating, 16 reviews

Private Studio- Great location!

Apr 1 – 8

$69 per night
Guest favorite

Home in Windsor

4.94 out of 5 average rating, 66 reviews

Gourmet Kitchen in Wine Country w/Hot Tub + Office

Apr 1 – 8

$489 per night
Guest favorite

Home in Healdsburg

5.0 out of 5 average rating, 8 reviews

The Dragonfly Healdsburg

Mar 15 – 22

$766 per night
Guest favorite

Guesthouse in Healdsburg

5.0 out of 5 average rating, 30 reviews

Bucher Vineyard Cottage

Aug 1 – 8

$250 per night
Guest favorite

Home in Healdsburg

4.98 out of 5 average rating, 47 reviews

Hidden Oasis ~ a Private Luxury Home in Healdsburg

Jan 9 – 16

$900 per night

Quick stats about vacation rentals in Windsor

Total rentals

350 properties

Rentals with dedicated workspaces

160 properties have a dedicated workspace

Rentals with a pool

230 properties have a pool

Pet-friendly rentals

60 properties allow pets

Family-friendly rentals

250 properties are a good fit for families

Total number of reviews

11K reviews

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Windsor?

    Yes! Work meets play with ease at over 160 vacation rentals in Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Windsor?

    Four-legged friends are welcome in Windsor. Choose from more than 60 vacation rentals for guests traveling with pets.

  • Are there Windsor vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 230 vacation homes with pools in Windsor, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in apartment rentals in Windsor?

    Experience the best of Windsor with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do condo rentals in Windsor have a gym?

    Absolutely! We offer over 100 condo rentals with a gym in Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Windsor have self check-in?

    Absolutely! We offer over 50 apartment rentals with self check-in in Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Windsor have a bbq area?

    Absolutely! We offer over 50 apartment rentals with a bbq area in Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Do serviced apartment rentals in Windsor have wifi?

    Absolutely! We offer over 40 serviced apartment rentals with wifi in Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly condo rentals in Windsor?

    Windsor has more than 90 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Windsor?

    Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with self check-in, over 10 homes with a gym, over 120 homes with wifi, over 60 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. California
  4. Sonoma County
  5. Windsor